4 definitions
by
Lil' Shammie

A weekend in which a man dresses in women's clothing and assumes a female identity in order to determine whether or not he would enjoy being a woman. Inspired by the movie "Tootsie" starring Dustin Hoffman.

Not to be confused with a Doubtfire holiday in which a man dresses as a woman to secretly spend time with his children.

1.)
Brett: Hey, man! You wanna come over on Saturday and play "Call of Duty"?
Marty: No, thanks. I'm gonna do a Tootsie weekend.

2.)
Devin: Do you like mascara?
JJ: Yeah, I kinda do. I think I'm gonna do a Tootsie weekend.

A: So you tricked your girlfriend's parents to hide in her closet?
B: Yeah, I told them it was for a surprise party.
A: And then what happened?
B: I went in there and had sex with her, and her parents didn't know what to do, so they just stayed in that closet.
A: Are you serious?! Then what?
B: I opened the door and yelled "SURPRISE!" No one knew what to do.
A: That's fucked up, man.
B: Sex prank.
A: Are you two still together?
B: No, the relationship ended immediately.